You know those celebs, the ones who always seem to be poolside in Santorini, riding elephants in Phuket or on a yacht off the coast of Saint-Tropez? Issa Rae is definitely not one of those celebs. “I haven’t had a vacation in a year,” she says. “I would, but I just haven’t had any time!” Lest this comment be misconstrued: Rae is definitely not complaining. She’s been happily working on her hit HBO television series Insecure (which she writes, stars in and executive produces), launching her film career (including a role in The Hate U Give, which premiered at the Toronto International Film Festival in September), killing it as a CoverGirl ambassador, and hosting high-profile events like the Council of Fashion Designers of America Awards.
Rae does, however, understand the importance of taking time off—especially when it comes to helping with her creative flow. (FYI: Studies show that travel, new experiences and giving your brain a rest, are all good for the imagination). “So much of being a creative is being inspired,’ she says. So what inspires her? Art, for one. We met at the Amex Live Life Experience pop-up on Queen Street West in Toronto—Rae spoke at the gallery on opening day—which is brimming with interactive installations from some of city’s buzziest artists, such as birdO and Christina Mazzulla. “An exhibition like this leaves you feeling charged,” says Rae. “It’s a reminder that you have to live your life. Or else, it’s pointless. You’re in hamster wheel of nothingness.”
Like all of us, it took Rae a while to get to this stage of self-awareness. After graduating from Stanford, she worked a series of odd jobs in her 20s. “I would do videography for weddings and high school and middle school talent shows, editing. I would tutor. I would babysit. In addition to having a full-time job. I would do a lot of temp work,” she says, listing off all of side hustles that helped her support her web series, Awkward Black Girl, which debuted in 2011.
Even if you’re not about to leave your nine to five, Rae stresses the importance of “trying to find what you love about a job.” “It still goes back to finding inspiration,” she says. “If you’re not happy there, take on a new project or reinvigorate life into a specific role. Or, look elsewhere. Find what makes you happy.” Including, I ask, “A vacation? Some work-life balance?” She smiles. “I know, I know. I’m working on that.”
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